Hydrochloric Acid → (4'-Butoxy[1,1'-biphenyl]-4-yl)boronic acid

HRID 1872382Notes

Reaction equation

HRID 1872382 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.C([O:27][B:28](OC(C)C)[O:29]C(C)C)(C)C.Cl>O1CCCC1.CCCCCC>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:28]([OH:29])[OH:27])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 211822924-Bromo-4'-butoxy-1,1'-biphenylHCID 178418339Butyllithium

Product 1

HCID 21182485(4'-Butoxy[1,1'-biphenyl]-4-yl)boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 4-bromo-4'-n-butyloxybiphenyl (3.05 g) in tetrahydrofuran (60 ml) was added 1.55M n-butyllithium in n-hexane (7.74 ml) at -60° C. over a period of 10 minutes. The solution was stirred at -30° C. for 1.5 hours and cooled to -60° C. To the solution was added triisopropylborate (3.46 ml) over a period of 5 minutes, and the mixture was stirred for 1.5 hours without cooling. To the solution was added 1N hydrochloric acid (20 ml) and the solution was stirred for 30 minutes and extracted with ethyl acetate. The organic layer was separated and washed with water, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with n-hexane. The solid was collected by filtration and dried under reduced pressure to give 4-(4-n-Butyloxyphenyl)phenylboronic acid (2.31 g).

Workup

  1. temperaturecooled to -60° C
  2. stirringthe mixture was stirred for 1.5 hours
  3. temperaturewithout cooling
  4. stirringthe solution was stirred for 30 minutes
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water, brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvents were removed under reduced pressure
  10. customthe residue was triturated with n-hexane
  11. filtrationThe solid was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-b8c8eea3f62c4739a6c00ea16ad05e18
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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